245356-50-7Relevant academic research and scientific papers
Control of remote stereochemistry using phosphine oxides: Formal synthesis of any stereoisomer diol (RR, RS, SR or SS) bearing 1,5-reIated stereogenic centres across an E double bond
Nelson, Adam,Warren, Sluart
, p. 1983 - 1998 (1999)
γ-Alkenyl β-hydroxy phosphine oxides have been epoxidised stereoselectively to give γ,5-epoxy β-hydroxy phosphine oxides with high anti stereoselectivity. The y-anisyl or γ-furyl ring of γ-aryl β-hydroxy phosphine oxides have been cleaved oxidatively to reveal a carboxylic acid and a ketone respectively. In the latter case, the ketone was reduced highly stereoselectively to give (4R*,5S*,6R*)-8-benzyloxy-6-diphenylphosphinoyloctane-l,4,5- triol as a single diastereoisomer with three controlled stereogenic centres. This method was then applied to the synthesis of three of the diastereoisomers of 8-benzyloxy-6-diphenylphosphinoyldodecane-l,4,5-triol with four controlled stereogenic centres; the middle two stereogenic centres were removed using an -selective Horner-Wittig elimination to give either diastereoisomer of 8-benzyloxydodec-5-ene-l,4-diol with 1,5-related stereogenic centres across an ￡alkene.
